(R)-N'-(5,8a-dimethyl-1,3,4,7,8,8a-hexahydro-6H-spiro[naphthalene-2,2'-[1,3]dioxolan]-6-ylidene)-4-methylbenzenesulfonohydrazide | 294202-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (R)-N'-(5,8a-dimethyl-1,3,4,7,8,8a-hexahydro-6H-spiro[naphthalene-2,2'-[1,3]dioxolan]-6-ylidene)-4-methylbenzenesulfonohydrazide
• CAS: 294202-68-9
• 化学式: C₂₁H₂₈N₂O₄S
• 分子量: 404.53
• InChiKey: DSNORJDJWRLNEW-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  76.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-N'-(5,8a-dimethyl-1,3,4,7,8,8a-hexahydro-6H-spiro[naphthalene-2,2'-[1,3]dioxolan]-6-ylidene)-4-methylbenzenesulfonohydrazide 在 3,5-二甲基吡唑 、 chromium(VI) oxide 、 甲基锂 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 氯仿 为溶剂， 反应 10.75h， 生成 (4'aR,8'aS)-5',8'a-dimethyl-3',4',4'a,8'a-tetrahydro-1'H-spiro([1,3]dioxolane-2,2'-naphthalene)
  参考文献：
  名称：

  Efficient, Highly Enantioselective Synthesis of Selina-1,3,7(11)-trien-8-one, a Major Component of the Essential Oil of Eugenia uniflora

  摘要：

  The first synthesis of selina-1,3,7(11)-trien-8-one (1), a major constituent of the essential oil from the leaves of Eugenia uniflora, has been accomplished, with excellent stereo- and regiocontrol, in eight steps and in 12% overall yield from the known octalone derivative 2a.

  DOI：

  10.1021/np000065f
• 作为产物：
  描述：

  对甲苯磺酰肼 、 (R)-5',8'a-Dimethyl-1',3',4',7',8',8'a-hexahydrospiro[[1,3]-dioxolane-2,2'-naphthalen]-6'-one 以 四氢呋喃 为溶剂， 反应 3.5h， 以100%的产率得到(R)-N'-(5,8a-dimethyl-1,3,4,7,8,8a-hexahydro-6H-spiro[naphthalene-2,2'-[1,3]dioxolan]-6-ylidene)-4-methylbenzenesulfonohydrazide
  参考文献：
  名称：

  Efficient, Highly Enantioselective Synthesis of Selina-1,3,7(11)-trien-8-one, a Major Component of the Essential Oil of Eugenia uniflora

  摘要：

  The first synthesis of selina-1,3,7(11)-trien-8-one (1), a major constituent of the essential oil from the leaves of Eugenia uniflora, has been accomplished, with excellent stereo- and regiocontrol, in eight steps and in 12% overall yield from the known octalone derivative 2a.

  DOI：

  10.1021/np000065f